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Billion-Dollar Deals in Drawstring Pants: A 'Succession' Fashion Retrospective

The stealth-wealth costumes help depict the dynamic Roy family power rankings.

Warning: Spoilers for all four seasons of “Succession” below.

In March, “Succession” began rolling out its fourth and final season, not with a bang, but rather a full-blown detonation. It was more of a pointed attack, really — on the “ludicrously capacious” (and nearly $3,000) Burberry bag that Tom Wambsgans railed into upon catching sight of it at an upper-crust birthday party.

Naturally, Tom’s critiques — “What’s even in there, huh? Flat shoes for the subway?” — resonated as much online as they did off. The episode led to a 310% uptick in Google searches for “Burberry Tote Bag,” according to 3DLook, a virtual fitting room company. Meanwhile, the dialogue itself has been memed so much that the memes themselves have become other memes.

But thematically, there’s more to the scene than Tom methodically obliterating one of fashion’s most iconic fashion houses.

“In the universe of the show, [Bridget, Cousin Greg’s date and the woman carrying the bag in question] probably thought, ‘I’m going to a party with rich people, so I’m going to bring my fancy bag,'” says Jake Woolf, a writer for GQ who has covered the fashion on “Succession” since its second season. “Obviously, Tom is referencing the size of the thing, first and foremost, but a giant Burberry check print isn’t how they do things in their world. It’s more about the $10,000 bag with no logos on it.”

Indeed, the fashion on “Succession” is flawlessly and at times bitingly true to that of the über-billionaire class. The clothing is approachable, at least in theory, yet wholly unattainable — “stealth wealth,” if you will. 

Costume designer Michelle Matland (who was unavailable for an interview) has built characters’ entire closets on the cashmere backs of Loro Piana and Tom Ford, like the rest of us may do with Uniqlo or Levi’s. This makes for an accurate portrayal of the super-rich, yes, but where does the depiction of reality end and the show’s storytelling begin? 

Across four seasons, Matland has used clothing to evolve individual character arcs on “Succession,” as the core trio of Roy siblings (among other ancillary figures like Connor, Tom or even Cousin Greg) vie for the position of the next Waystar RoyCo CEO.

“The costumes say a lot about their relationship to their father,” says Ruth Etiesit Samuel, a culture reporter at HuffPost, where she runs a costume and styling column called “Who’s Behind the Clothes.” “As they’re ebbing and flowing in the Roy family power rankings, you see how their style changes.”

Shiv commands the Roy siblings at Connor’s rehearsal dinner in an Altuzarra suit and Lafayette 148 New York blouse. 

Photo: Macall B. Polay/HBO

Since “Succession”‘s very first season, fashion has been an inescapable player upon which the Roys project their innermost aspirations. And with the exception of a few more obvious moments (when the then-prodigal Kendall wears Lanvin sneakers to impress the founders of an art startup in a season one episode, for instance), the clothes, though always expensive, have also tended to be inconspicuous. As Samuel explains, that’s kind of the point.

“It’s coded luxury, in the sense that the rich are always trying to downplay how much wealth they have,” she says. “They’re not interested in gaudy luxury. We see a lot of these very subtle pieces that are, let’s say, a T-shirt, but it’s by Margiela, and you’d have no clue until you look it up.”

This isn’t just a hypothetical example. During a pivotal lunch among Roy siblings in the season-three finale, Kendall wears a completely ordinary T-shirt that fashion folks — including the Instagram account @successionfashion, — quickly identified as being Margiela’s $340 Stereotype tee. “It” girl PGM board member Naomi Pierce is another winning case study here: “She wears a lot of Proenza Schouler,” says Samuel, “but half the time, she looks like she’s in pajamas.”

Back to Kendall’s Margiela tee, which, in that lunch scene, he topped off with a hefty $15,500 necklace designed by contemporary artist Rashid Johnson. The pendant itself features one of Johnson’s acclaimed “Anxious Men” paintings — a fitting nod to Kendall’s turbulent season of coup attempts and brushes with death. Especially in such moments of crisis, Kendall’s meticulously curated image speaks the loudest of his siblings, and has since the very first season. (Again with the Lanvin sneakers.)

“Whenever Kendall is trying to get out from under his father, whenever he seems to be going through it, he tends to adopt this urban, culture-vulture, Black-adjacent aesthetic, with bomber jackets and big chains,” says Samuel.

Take Kendall’s collection of status baseball caps — namely, the $625 cashmere-blend number by ultra-luxury Italian label Loro Piana he wore to his brother Connor’s rehearsal dinner, of all places. “Succession” lives and breathes by these nods to the Roys’ 0.1%-type wealth; coats are almost never worn, simply because they get driven everywhere.

“Maybe that upper crust of society wants to feel more like an everyman by wearing a baseball hat,” says Woolf. “But if they’re going to wear a baseball hat, it’s not going to be one they got from a gift shop — it’s going to be the one that was probably at Bergdorf Goodman.”

PGM “It” girl Naomi Pierce in a Proenza Schouler leather-trimmed top with the birthday boy, Kendall Roy, in a Gucci bomber jacket and Rashid Johnson necklace.

Photo: Macall B. Polay/HBO

Kendall’s little brother Roman, meanwhile, is more consistent with his costuming. Across all four seasons, his aesthetic has been more in line with that of a Silicon Valley bro than a New York City corporate bulldog — a ploy he may believe will help get him the CEO title in the end. 

“He wants to present as cool, calm and collected, but in reality, he does care about his father’s approval,” says Samuel.

Rarely wearing a jacket or even a tie, Roman can more often be found in button-down shirts and everyday (i.e. not dress) pants. His accessories are just as pedestrian: While in Italy in season three, Roman’s shoes of choice were a $120 pair of tennis shoes from Cole Haan — a mall steal compared to Kendall’s $335 Dries Van Noten hiking boots or $890 Gucci sneakers.

And then there’s Shiv, whose fashion has gotten progressively worse (but more expensive) as the show went on and she became more involved in the family business. Now, it’s not necessarily that the clothes themselves are bad — it’s only in the styling (or lack thereof) that they become a problem.

The season four premiere saw Shiv making a literal $10-billion deal in drawstring silk trousers (albeit $555 ones from Max Mara) and a Skims bodysuit. On paper: great — for happy hour at the Amanyara beach club. By the end of the episode, as a newly-separated Shiv goes to collect her dry cleaning from the home she once shared with Tom, said pants were creased and sloppy, somehow even sadder than they were at the episode’s start. Where was her wardrobe stylist? Hell, even Kerry is wearing Sergio Hudson these days.

Shiv making a $10-billion deal in Max Mara trousers and a Skims bodysuit.

Photo: Claudette Barius/HBO

“For so much of her life, Shiv has been in this position where her family has been calling the shots, and fashion is possibly the one place she feels like she could have some semblance of control,” says Samuel.

At the start of the series, though, Shiv was in a position of control. When we first met her, the only Roy daughter was deeply entrenched in the Washington, D.C. circuit as a hot-shot political consultant, sporting long, wavy hair and oversized cardigans. Yet by season two, she’s sliced her hair into a blunt bob and traded her kischy knits for generic suiting courtesy of Polo Ralph Lauren and Armani

“She wants to make her presence known,” says Samuel, “and she thinks that by doing all these things, adopting a more corporate, but also a bit more rigid and masculine aesthetic, by being married, by being the stable one, that, yes, she will get the throne.”

So, will she? Samuel, for one, is skeptical, and largely because of the ways we’ve seen her evaporate into Waystar altogether.

“I feel as though Logan doesn’t like his daughter,” says Samuel. “He probably believes, apart from apparent misogyny, that she’s in way over her head, that she’s too much of a rule-follower and thinks that she can do everything herself. Shiv is the type that doesn’t want to let anyone in.”

This also means she doesn’t want anyone else to control her image — which is where those crinkled cabana pants reenter the picture. It’s a difficult pill to swallow: With all those billions (“piles” of them, to quote Logan directly) and thereby unfiltered access to beautiful things, is this truly what billionaires are wearing?

“This group of people have the means to get their entire wardrobes from these really, really high-end luxury brands, and are perfect customers because they don’t ask a lot of questions and just hand over their credit card,” says Woolf. “That doesn’t necessarily render the most stylish looks at the end of the day. But it is interesting to observe.”

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